Tert-butyl 4-cyanopiperidine-1-carboxylate → Tert-butyl 4-cyano-4-[3-(methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate
Reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:12]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)#[N:13].C[Si](C)(C)[N-][Si](C)(C)C.[K+]>>[C:12]([C:14]1([C:2]2[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)#[N:13]Participants
4
Procedure
2-Chloro-3-methoxymethoxy-pyridine (Tetrahedron 58 (2002), 309-314) (2 g, 11.5 mmol) and tert-butyl 4-cyanopiperidine-1-carboxylate (1.6 g, 7.7 mmol) were reacted in the presence of potassium hexamethyldisilazide (9.2 mmol) using the method in example 8-1 to afford the desired product: tert-Butyl 4-cyano-4-[3-methoxymethoxy)pyridin-2-yl]piperidine-1-carboxylate: 1H NMR δ (ppm)(CDCl3): 8.21 (1 H, d, J=4.6 Hz), 7.53 (1 H, d, J=8.3 Hz), 7.27-7.23 (1 H, m), 5.31 (2 H, s), 4.20 (2 H, br s), 3.55 (3 H, s), 3.28 (2 H, br s), 2.35 (2 H, s), 2.10 (2 H, br s), 1.47 (9 H, s).
Sources & evidence
- ORD record
- ord-7d614aab57e743a2bd1f5bacaf156b73
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825135B2
Reaction notes
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